EP0558096A1 - Verfahren zur Herstellung von Dichlor-(2,2)-Paracyclophanen - Google Patents

Verfahren zur Herstellung von Dichlor-(2,2)-Paracyclophanen Download PDF

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Publication number
EP0558096A1
EP0558096A1 EP93106300A EP93106300A EP0558096A1 EP 0558096 A1 EP0558096 A1 EP 0558096A1 EP 93106300 A EP93106300 A EP 93106300A EP 93106300 A EP93106300 A EP 93106300A EP 0558096 A1 EP0558096 A1 EP 0558096A1
Authority
EP
European Patent Office
Prior art keywords
solution
paracyclophane
dichloro
quaternary ammonium
reaction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP93106300A
Other languages
English (en)
French (fr)
Other versions
EP0558096B1 (de
Inventor
Hiroshi Maruyama
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daisan Kasei Co Ltd
Original Assignee
Daisan Kasei Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP34223089A external-priority patent/JPH0747553B2/ja
Priority claimed from JP10171590A external-priority patent/JPH0739359B2/ja
Application filed by Daisan Kasei Co Ltd filed Critical Daisan Kasei Co Ltd
Publication of EP0558096A1 publication Critical patent/EP0558096A1/de
Application granted granted Critical
Publication of EP0558096B1 publication Critical patent/EP0558096B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/92—Systems containing at least three condensed rings with a condensed ring system consisting of at least two mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic system, e.g. cyclophanes

Definitions

  • X is a halogen such as chlorine or bromine.
  • 2 or 3 hereinafter referred to as 2(3) )-chloro-p-methylbenzylhalide is prepared by chlorination of monochloro-p-xylene or by chlorination of p-methylbenzylhalide. Then it is reacted with trimethylamine to obtain 2(3)-chloro-p-methylbenzyltrimethylammonium halide ( hereinafter referred to as chlorinated quaternary ammonium salt ).
  • chlorination can be greatly simplified with excellent yields and needing no further refining process.
  • the chlorination is conducted by feeding chlorine gas into an aqueous solution of the quaternary ammonium salt.
  • the aqueous solution heated through exothermic reaction is cooled to keep a moderate temperature range between 0 o C and 60 o C.
  • Higher temperature than 60 o C causes side reaction resulting in low product yields and lower temperature than 0 o C often results in precipitation of the quaternary ammonium salt, thereby disturbing sufficient mixing for reaction.
  • Termination of the reaction can be detected by gaschromatographic analysis through the following reaction under elevated temperature: wherein X is a halogen such as chlorine or bromine.
  • Chlorine gas feeding is stopped at the time no p-methylbenzyl halide can be detected by gaschromatographic analysis of the reaction solution. Excess chlorine in the solution is to be expelled by passing an inert gas such as nitrogen through the solution.
  • An aqueous solution of the chlorinated quaternary ammonium salt thus obtained which is an intermediate in the preparation of dichloro-(2,2)-paracyclophane, is then subjected to successive reaction.
  • Dichloro-(2.2)-paracyclophane can be prepared with improved yields by conducting Hofmann reaction of the chlorinated quaternary ammonium hydroxide prepared in situ by the action of alkali metal hydroxide on the chlorinated quaternary ammonium salt, in the presence of dioxane.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP93106300A 1989-12-29 1990-12-28 Verfahren zur Herstellung von Dichlor-(2,2)-Paracyclophanen Expired - Lifetime EP0558096B1 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP34223089A JPH0747553B2 (ja) 1989-12-29 1989-12-29 ジクロロ―（２，２）―パラシクロファンの製造方法
JP342230/89 1989-12-29
JP101715/90 1990-04-19
JP10171590A JPH0739359B2 (ja) 1990-04-19 1990-04-19 ジクロロ‐（２，２）‐パラシクロファンの製造方法
EP90125764A EP0436957B1 (de) 1989-12-29 1990-12-28 Verfahren zur Herstellung von Dichlor-(2,2)-paracyclophan

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
EP90125764.2 Division 1990-12-28

Publications (2)

Publication Number Publication Date
EP0558096A1 true EP0558096A1 (de) 1993-09-01
EP0558096B1 EP0558096B1 (de) 1996-03-20

Family

ID=26442542

Family Applications (2)

Application Number Title Priority Date Filing Date
EP90125764A Expired - Lifetime EP0436957B1 (de) 1989-12-29 1990-12-28 Verfahren zur Herstellung von Dichlor-(2,2)-paracyclophan
EP93106300A Expired - Lifetime EP0558096B1 (de) 1989-12-29 1990-12-28 Verfahren zur Herstellung von Dichlor-(2,2)-Paracyclophanen

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP90125764A Expired - Lifetime EP0436957B1 (de) 1989-12-29 1990-12-28 Verfahren zur Herstellung von Dichlor-(2,2)-paracyclophan

Country Status (4)

Country Link
US (1) US5679874A (de)
EP (2) EP0436957B1 (de)
CA (1) CA2032714C (de)
DE (2) DE69026119T2 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6743575B2 (en) 1996-06-14 2004-06-01 Biostore New Zealand Ltd. Compositions and methods for the preservation of living tissues
CN107216232A (zh) * 2017-06-05 2017-09-29 昆山彰盛奈米科技有限公司 一种派瑞林f的制备方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5302767A (en) * 1993-03-26 1994-04-12 Union Carbide Chemicals & Plastics Technology Corporation [2.2] paracyclophane and derivatives thereof
JP3773065B2 (ja) * 1995-08-25 2006-05-10 第三化成株式会社 ジクロロ−テトラフルオロ−［２，２］−パラシクロファンおよびその製造方法
CN106986742B (zh) * 2017-04-05 2020-08-04 常州市骏佳化工有限公司 四氯代对二甲苯环二体合成方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0253191A1 (de) * 1986-06-27 1988-01-20 Montedison S.p.A. Verfahren zur Herstellung von (2,2)-Paracyclophan und dessen Derivaten
US4849559A (en) * 1987-05-15 1989-07-18 Union Carbide Corporation Process for the preparation of dichloro-[2,2]paracyclophane

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB807196A (en) * 1955-05-02 1959-01-07 Du Pont Polyarylenethylenes and their copolymers
DE3561389D1 (en) * 1984-03-07 1988-02-18 Ihara Chemical Ind Co Process for producing a halobenzene
IT1191633B (it) * 1985-10-30 1988-03-23 Montedison Spa Procedimento per la preparazione di (2,2)-paraciclofani alogenati e miscele di (2,2)-paraciclofani alogenati ottenuti
IT1190647B (it) * 1986-06-27 1988-02-16 Montedison Spa Processo per la preparazione di (2,2)-paraciclofano e suoi derivati
IT1203876B (it) * 1987-04-10 1989-02-23 Montedison Spa Processo per la preparazione di (2,2)-paraciclofano e suoi derivati

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0253191A1 (de) * 1986-06-27 1988-01-20 Montedison S.p.A. Verfahren zur Herstellung von (2,2)-Paracyclophan und dessen Derivaten
US4849559A (en) * 1987-05-15 1989-07-18 Union Carbide Corporation Process for the preparation of dichloro-[2,2]paracyclophane

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6743575B2 (en) 1996-06-14 2004-06-01 Biostore New Zealand Ltd. Compositions and methods for the preservation of living tissues
CN107216232A (zh) * 2017-06-05 2017-09-29 昆山彰盛奈米科技有限公司 一种派瑞林f的制备方法

Also Published As

Publication number Publication date
CA2032714A1 (en) 1991-06-30
DE69005092D1 (de) 1994-01-20
DE69026119D1 (de) 1996-04-25
DE69005092T2 (de) 1994-04-28
EP0436957B1 (de) 1993-12-08
EP0436957A1 (de) 1991-07-17
CA2032714C (en) 1999-01-26
DE69026119T2 (de) 1996-08-29
US5679874A (en) 1997-10-21
EP0558096B1 (de) 1996-03-20

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